Hamlet is best known for its exploration of melancholy, yet it can also be read as a meditation on the good life, as negative reflection upon utopia. The play’s account of suffering bears upon the nature of happiness, even if the latter is largely absent. Rephrasing Dover Wilson’s famous question about the play, this chapter explores Hamlet’s preoccupation with the relationship between event, chance, and emotion. Through a close examination of Shakespeare’s use of the terms hap, perhaps, and happy, it argues that Hamlet imagines happiness as serendipity, or the evasion of conventional moral goods and totalising social systems. In the early modern period the primary meaning of happy was not a feeling of pleasure, but rather, ‘Having good “hap” or fortune; lucky, fortunate; favoured by lot, position, or other external circumstance’ (OED, 2a). By examining the play’s exploration of this notion, the chapter sees Hamlet’s study of political repression as part of a broader thesis: that happiness lies in hap (suddenness, spontaneity, chance) rather than bureaucratic prescription. The conditions for this kind of utopian freedom, however, are difficult to achieve, and the play’s tragic sting can be read in this light.